Date: Thu, 2 Mar 2000 11:23:20 -0700
From: Jim Johnson
Subject: Jim's Discovery
I was 16 years old when I had my first man. He was the man who turned me
on to the fact that I was gay, feminine and a crossdresser. I had always
felt more attracted to boys than girls and had many girl friends and few
boy friends and this is my true story.
That summer I found a job cleaning a ladies lingerie store for a wonderful
gentleman I will call Bill for this story. I had always tried to be a boy,
I played hockey, football and baseball. I did all the "boy" things but was
always out of place. In truth I was always small, girly and feminine no
matter how hard I tried. It was who I was and Bill was the first to
acknowledge this.
I had been working there about a week and every night Bill watched me. I
liked him watching me because he seemed so much like me. Soft, feminine
not hard and mannish. He too was on the thinner side, soft features, long
blond hair. I should tell you about me, I was about 5-4 then maybe 125 lbs
and had long medium brown hair. I had a nice curved ass and was well hung
even then, almost 8 inches. Today I am still small only 5-9 and 165 lbs
but that suits who I am.
Bill one night asked, "Ever try on women's clothes?"
"No," I replied trying to sound indignant, "of course not!"
Bill laughed, "It's ok Jimmy, I have lots and I think you would look great
al dressed up."
He picked out a nice b cup bra, matching panties and a see through top and
short skirt. He handed the items to me and started to get me undressed. I
stepped back but he just smiled and continued.
"It's ok Jim, I won't tell anyone, honest."
So I let him because it really excited me to do it. I had gotten into my
Mom's and sister's clothes so often and imagined a nice man kissing me. I
had always felt ashamed at my gay fantasy and being dressed up, even though
I always orgasmed. Bill got me naked and my cock was stiff, no one had
ever seen it hard before.
"Nice piece." He said looking at my hardness. "You know it's not fair your
naked and I'm not."
So he took off his shirt and pants and just the sight of him naked got me
even harder. I could feel pre-cum oozing from the tip of my cock. I was
feeling wonderful as he moved closer to me.
"You can't try on lingerie and dresses with this." And he bent down and
took my cock inot his experienced mouth. I thought I died it was so
beautiful,the feel of his wet tongue working the bottom of my piss slit
lapping up my cum. I couldn't hold back and I just shot a huge load into
his mouth.
"There, that's better isn't it Jim?" All I could do is nod my approval. I
took the clothes and put them on. I looked in the mirror and damn I looked
pretty good. My ass filled out skirt nicely. Bill took some nylons and
shoved them in my bra to give the look of cleavage. Then he got some
make-up and applied it to my face, he did my nails and the next time I
looked in the mirror I looked nothing like a boy.
Then he did the really unexpected, he dressed in ladies wear as well.
After he put on his makeup we were ready.
"Come on I know a great club where we can go."
Go, go? How the hell could we go anywhere, wouldn't someone see? But go we
did, we went to a private club and no one seemed to notice we were men.
There was dancing and drinks and we had a great time. After we left I held
his/her hand and told him how much fun I had.
"I'm glad Jim because I need you, I must admit I had this planned because I
called your parents and said you needed to stay over as I had work for you
early."
I was shocked, planned? Just then he kissed me, full on the lips, tongue
deep in my mouth. His hands cupped my ass lifting the skirt just a bit.
We got in the car and went to his place. Climbing the stairs I was so hot,
my cock strained at the panties. Bill stopped at the top and dropped his
panties and lowered my head to his cock. I could smell his musky scent and
my cock got harder. My lips were dripping drool as I took it into my
mouth. I sucked pullling his ass into me, I lost myself in it. Then he
came, shooting a delicious load down my throat. I sucked and sucked until
I could not get anymore.
We went inside and stripped off the girls clothes and my cock bounced out,
his had recovered already. We went to his room and lay on the bed kissing
touching and generally feeling each other up.
"I want your ass Jimmy, I need to feel that tight ass around my cock."
"Yes Bill take it, please?"
Bill got some lube and I smeared it all over his cock while he worked my
asshole. I had used things in it but this was going to be my first man.
Bill was gentle, easing his cock into my tight hole. IT felt so good to
feel it slide in. It was bigger than mine and at first I was scared. But
he stroked my thighs and butt cheeks and I relaxed as he began to fuck me.
He went harder and faster until I could feel his cock contract and shoot it
deep in me. When I felt it hit my walls I came all over the sheets leaving
a big wet spot.
Bill rolled off and kissed me, letting his covered cock lean against his
fine feminine leg. I loved the fucking, the sucking, the cum. I could
never get enough cum., the rest of the summer I had poor Bill fucking me
every day. Luckily he introduced me to his men friends. They all liked
the idea of fucking someone so young. Oh yeah Bill was 45.
I hope you liked my telling of my first time. If you drop me a note I
would love to share more.
Jim